A list by Anna Pinto & Ted Valentin. Updated February 2024.
We have created a list with the best castle hotels near Gaiole in Chianti, Italy. We have also included hotels in old "castello"-s, historic properties, country estates, palaces, historic villas, french "relais" (mansions), hamlets, resorts, beautiful country residences, monasteries, old manor houses and old palaces. Hope you enjoy it. We think it might be the best of its kind around. Tip: Set your dates to see room prices!
Unique. Good breakfast. Set on a hill overlooking the Massellone Valley, the historic and elegant Castello Di Meleto is 2 km from Gaiole in Chianti. It offers rooms and apartments with Tuscan-style furnishings. The Meleto Castle features large green areas with 2 swimming pools, barbecue facilities and bowling green. Castello Di Meleto is 30 minutes’ drive from Siena and Rapolano Terme. The accommodation features exposed wood beams, terracotta floors and wooden furniture. The basic rooms include a private bathroom. The apartments also have a kitchenette. Free Wi-Fi is provided at the reception, and free private parking is available too. Arezzo is 55 km away.Show full description
A beautiful 13th-century castle between Siena and Florence has AMAZING facilities, including two infinity pools, an aromatic garden, and a wine shop. In addition, the on-site restaurant serves delicious food options.
Outstanding SPA facilities. Set in Tuscany's countryside, Castello di Spaltenna Exclusive Resort & Spa is an ancient monastery from the 10th century. It offers 2 swimming pools, one of which is heated, a restaurant and spacious rooms with Sky TV. Rooms at the Castello Di Spaltenna have traditional Tuscan décor and panoramic views over the valley or the courtyard. Il Pievano restaurant is situated in the castle’s historic hall and offers a large wine list including many wines from the local Chianti region. They all include free Wi-Fi. The outdoor pool has a waterfall and a sun terrace for guests to sunbathe. In the winter months, there is the indoor pool with countryside views. Candlelit dinners are served out on the courtyard. A sauna, Turkish bath and gym, tennis court and billiard room are also available. Staff can advise on the many hiking and mountain biking trails in the area.Show full description
A historical heritage monastery in the Chianti region with luxuriously designed rooms and a great pool area with panoramic views of the valley below. There is also a Michelin-star restaurant with excellent local cuisine.
Charming. Cosy rooms. Popular among couples. Surrounded by olive groves and vineyards in the heart of the Chianti region, Castello di Volpaia offers rustic rooms and a apartment with a kitchen and free Wi-Fi. Located in the medieval hamlet Volpaia, it features an outdoor pool. Guests can enjoy wine tastings, take cooking classes. The Volpaia provides free private parking, and is well placed for walking in the Tuscan countryside. Siena is 35 km away, and Florence can be reached by car in 1 hour.Show full description
An absolutely gorgeous hotel within an old refurbished castle with several good restaurants practically on your doorstep. It also has a cozy pool area with stunning views and exceptional rooms with great attention to detail.
Great restaurant. Castello Di Tornano Wine Relais is located on a hillside in the Chianti Classico wine region. It offers free WiFi, free parking, and rooms and apartments with satellite TV and bathroom. The restaurant at the Castello Di Tornano Wine Relais serves Tuscan specialities and classic Italian cooking. The Castello Di Tornano Wine Relais is 18 km from Siena. Rooms are air conditioned and include a minibar. The apartments offer a fully fitted kitchen. The swimming pool is set in gardens and surrounded by trees. There is a tennis court, and guests can also enjoy massage treatments under previous request.Show full description
Great value. Popular among couples. A historic castle dating back to the 14th century, the Castello Di Gabbiano is set amongst 100 hectares of olive groves and vineyards. The rooms come in a Tuscan Renaissance style. Breakfast at the Castello includes Tuscan specialities, and is served in one of the drawing rooms or out in the garden. Florence is 22 km away. The property is a working farm, with trekking paths amongst the vineyards. The large garden is complete with outdoor swimming pool. The rooms are charming and elegant, and feature rustic terracotta floors and wooden furniture. Air conditioning is available in the summer. From April until November, lunch and dinner are available from Tuesday evening to Sunday evening at the restaurant 70 metres away. Wine tastings are organised daily.Show full description
Castello Di Gabbiano is a unique hotel in Mercatale Val Di Pesa. It is a castle with a winery and a restaurant on-site, surrounded by vineyards and olive groves. The rooms are in the castle and farmhouse, giving a historic and charming feel.
Elegant. Comfortable beds. Popular among couples. Castello La Leccia is a restored mediaeval hamlet, featuring an 11th-century castle, an outdoor swimming pool, and free Wi-Fi. The property is set on a hill, and offers a terrace with views of the Tuscan countryside. Castellina in Chianti is 2 km away. Castello La Leccia is at the end of an unpaved road off the SP51 road. Accommodation at La Leccia comes with a unique design and handmade furniture. Some rooms boast original stuccoes and four-poster beds. The restaurant serves traditional dishes of Tuscany, along with great local wines. The breakfast buffet features both sweet and savoury items, including homemade cakes, Tuscan bread, fresh fruit, cheese and cold cuts. The property organises tastings of its own wine and olive oil. Parking is free.Show full description
Charming. Superb interior design. Situated in Mugnana, 9.3 km from Piazza Matteotti, Castello di Mugnana features accommodation with a seasonal outdoor swimming pool, free private parking, a garden and a terrace. Featuring a bar, the property is located within 21 km of Piazzale Michelangelo. Castello di Mugnana offers some rooms that have a balcony, and every room is fitted with a coffee machine. Ponte Vecchio is 21 km from Castello di Mugnana, while Uffizi Gallery is 21 km from the property. This pet-friendly hotel also has free WiFi. At the hotel, the rooms have a desk, a flat-screen TV, a private bathroom, bed linen, towels and a patio with a garden view. All rooms will provide guests with a fridge. Guests at the accommodation will be able to enjoy activities in and around Mugnana, like cycling. The nearest airport is Florence Airport, 29 km from the hotel.Show full description
If you’re looking for a romantic and tranquil vacation, it might be the best option to stay! This 1000-year-old castle is beautifully renovated and has excellent facilities, like an outdoor pool, old-money charmed rooms, and an al-fresco breakfast is a perfect addition.
Great breakfast. Immersed in the Tuscan countryside between Siena and Florence, this 4-star hotel offers high-quality service on 20 acres of rich parkland, just outside of Monteriggioni. You can enjoy a peaceful and relaxing setting at Borgo San Luigi. This 17th-century palace is just 2 km from the motorways and set on an unpaved road. You can participate in a variety of sports on this rich, resort-like, country estate. Rest in the shade of the thick gardens, enjoy a swim in the Olympic-sized pool, or savour breakfast outdoors poolside during the summer. There is a tennis court and a football field. Go quad biking or horseback riding and explore the surrounding rural area. Borgo San Luigi has friendly, professional staff who can organise tours, excursions or team-building events, an ideal way to relax between meetings. Enjoy high-quality rooms with period furniture and Tuscan-style furnishings. Featuring vineyard or mountain views, rooms include rustic fire places, historic frescoes and Tuscan four-poster beds. Nearly all rooms offer a garden or a balcony. Savour typical Tuscan cooking at La Limonaia, the chic on-site restaurant at Borgo San Luigi. La Limonaia is suitable for a variety of events, including large receptions, ceremonies, banquets and business dinners. Borgo San Luigi is the perfect location to enjoy a unique holiday, where you can participate in a cooking school or English-language school.Show full description
Borgo San Luigi is a historic hotel in Monteriggioni, with elegant rooms and beautiful gardens. It provides a luxurious experience in a charming, 17th-century setting. The hotel's rich history and serene atmosphere set it apart from other accommodations in the area, making it a unique and memorable place to stay.
Beautiful. Tennis court. Surrounded by Tuscan olive groves and vineyards, Borgo Scopeto Wine & Country Relais offers 2 swimming pools and a bike rental service. Rooms have a contemporary design with free Wi-Fi and flat-screen TVs. The hotel's gastronomic restaurant serves Tuscan specialities and wines produced on the estate and in the surrounding area. From this restored 13th-century hamlet, you can explore the Chianti region or take a wine tasting tour. You can also enjoy wine and olive oil tasting. Rooms and suites at the Borgo Scopeto are spacious and decorated in calming colours. They are equipped with satellite TV and a minibar. The historic city of Siena is a 20-minute drive away. The Relais Borgo Scopeto also has a wellness centre with an indoor pool, Turkish bath and a hot tub, all available at an extra charge. 2 tennis courts are available free of charge.Show full description
Close to beach front. Delightful property. Stunning pool facilities. Set on the Valdarno Superiore hills to the south of Florence, I Bonsi is set in a fortified manor house dating back to the 15th century. The property features a park with outdoor swimming pool, and sun terraces with views of the Arno Valley. It was restored in a neo-Gothic style by the noble Budini Gattai family, who made it their residence in the 19th century. There is also a beautiful 17-century church. Agriturismo I Bonsi offers rustic apartments, which blend original architectural features and modern facilities. Each features a patio, and a fully equipped kitchen or kitchenette. Free Wi-Fi is available in the apartments and by the pool. The property is surrounded by vineyards and olive groves. You can visit the oil mill, and buy the olive oil and wine produced on site. Free parking is provided, and you can rent a bicycle at reception for free, and explore the estate and the area.Show full description
I think this place could be the most BEAUTIFUL country house in Florence. It also has lovely pool facilities, a barbecue area in the lush garden setting, and a charming dining room with a fireplace. SO NICE!
Unique. Great location. Castello di Gargonza is a privately owned Tuscan village offering accommodation from its hilltop location, between Arezzo and Siena. The Valdichiana Valley and a 500-hectare forest surround the village. Original terracotta floors and wood-beam ceilings are some of the original furnishings of Gargonza's apartments and rooms. To provide a relaxing environment, TVs are not available. Each type of accommodation is located throughout the village. Some have a fireplace and views over the valley. An outdoor pool, private gardens and a conference centre are all within the walls of this medieval property. St. Tiburzio and St. Susanna Church are also found here. La Torre di Gargonza restaurant is on site and open every day except on tuesdays. Homemade pasta and traditional Tuscan cuisine are served daily, while vegetarian, gluten-free and Jewish options are available on request.Show full description
Castello Di Gargonza is a beautifully restored 16th century hamlet located in the Tuscan hills. It is a secluded oasis of calm with great views, a lovely pool, and trails for walking and running.
Charming. Cosy rooms. Popular among couples. Borgo Vescine is located in the heart of Tuscany, right in the Chianti Classico area. The Relais has an extension of 100 acres and is 20 km from Siena and 42 km from Florence. Today, Borgo Vescine stands as a luxurious Relais, meticulously preserving the original charm of a medieval village and is surrounded by vineyards and olive trees. Guests have the opportunity to partake in a variety of authentic experiences, including exclusive wine tastings, hands-on cooking classes, exhilarating truffle hunts, scenic Vespa tours, and delightful al fresco dinners. Dinners are hosted among the olive trees or in the central square with the purpose of recreating the ancient time at the Borgo. This enchanting retreat offers: a wine room dated 1061 a.C., a heated outdoor swimming pool with stunning panoramic vistas, two distinctive bars and restaurants and a complimentary parking. Enjoy refined dishes on the open-air Terrace restaurant overlooking the Tuscan hills or experience nature firsthand at the Eco-Nature Bistrot. You will have the opportunity to sip drinks and cocktails in both the Borgo Vescine’s bars. The 28 rooms are all luxurious and decorated in classic tuscan dècor, some accommodations include a private balcony with views of the rolling hills, the forests, or the Borgo itself. Additionally, they are equipped with flat-screen TVs, free WiFi, and cozy bathrooms. Surrounded by lush gardens and verdant vegetation, Borgo Vescine also boasts its own vegetable garden, saffron fields, and lavender cultivation, adding to the allure of this idyllic retreat.Show full description
Il Borgo di Vescine is a charming hotel situated in a medieval village in the beautiful Chianti hills. The hotel provides unique accommodation in restored cottages, creating a cozy and stylish atmosphere.
Beach front location. Relaxing atmosphere. Amazing pool. Boasting a shared lounge and views of garden, Castello di Cafaggio is a villa set in a historic building in Impruneta, 15 km from Pitti Palace. This villa has a private pool, a garden and free private parking. For guests with children, Castello di Cafaggio features outdoor play equipment. Strozzi Palace is 15 km from Castello di Cafaggio, while Santa Maria Novella is 15 km from the property. Featuring family rooms, this property also provides guests with a picnic area. All units are fitted with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a bidet, a hair dryer and a wardrobe. Each unit is fitted with a kettle, a private bathroom and free WiFi, while some rooms are fitted with a terrace and some have pool views. At the villa complex, each unit is equipped with bed linen and towels. A selection of options including fresh pastries, fruits and juice is available for breakfast, and breakfast in the room is also available. Guests at the villa can make the most of yoga classes offered in-house. If you would like to discover the area, cycling, hiking and walking tours are possible in the surroundings and the accommodation can arrange a bicycle rental service. The nearest airport is Florence Airport, 21 km from the villa.Show full description
Castello di Cafaggio Borgo is a castle located in Impruneta, Italy, that offers visitors a unique and romantic experience. The castle is set up in a way that allows for privacy and quiet, while still providing incredible views of the surrounding scenery.
Highly elegant. Comfortable beds. Hotel Le Fontanelle enjoys panoramic views from its exceptional location in the Chianti Hills, 20 minutes drive from Siena. Relax and enjoy wellness and sports facilities in this peaceful location. Hotel Le Fontanelle's pretty main building dates back to the 13th century, part of an old country estate. All rooms have beamed ceilings and terracotta floors. They overlook the surrounding vineyards, woods, and valley. Modern facilities such as LCD satellite television and internet access are also provided. Enjoy a refreshing swim and stunning views in Hotel Le Fontanelle's outdoor pool or borrow one of the hotel's bikes free of charge, and go exploring the countryside. Guests can visit Tuscany from Hotel Le Fontanelle as the resort is located in the Chianti Region which is famous for sightseeing. Indoors you can work out in the gym, go for a swim in the indoor pool with hydromassage area or really pamper yourself and go to the wellness area. Relax in the sauna or the Turkish bath, or request one of a range of beauty treatments or massages. Hotel Le Fontanelle's La Colonna restaurant has a panoramic terrace and serves traditional Italian cuisine with a creative twist. Florence is 80 km from Hotel Le Fontanelle, while Siena is 20 km from the property. The nearest airport is Florence, 90 km from the hotel, and the property offers an airport shuttle service on request with extra charge.Show full description
I really like this place... I think it is one of the most ELEGANT luxury hotels in Gaiole in Chianti.
Beach front location. Lovely property. Superb breakfast. La Valletta Boutique Wine Estate has air-conditioned guest accommodation in Panzano, 10 km from Piazza Matteotti, 36 km from Pitti Palace and 37 km from Piazzale Michelangelo. This bed and breakfast features a pool with a view, a garden and free private parking. Guests at La Valletta Boutique Wine Estate will be able to enjoy activities in and around Panzano, like cycling. The nearest airport is Florence Airport, 43 km from La Valletta Boutique Wine Estate. The property offers services including meeting and banquet facilities and walking tours. At the bed and breakfast, some units have a private entrance, dining area, fireplace and dishwasher. The units come with a coffee machine, a TV, a safety deposit box and free WiFi, while some rooms come with a terrace and some have garden views. The units feature a private bathroom, free toiletries and bed linen. Buffet and continental breakfast options with warm dishes, local specialities and fresh pastries are available every morning at the bed and breakfast. There is a coffee shop and lounge. The bed and breakfast has a picnic area where you can spend a day out in the open. Ponte Vecchio is 37 km from the accommodation, while Uffizi Gallery is 37 km away.Show full description
Historic. Comfortable beds. Residenza D'Epoca Palazzo Buonaccorsi is a historical palace dating back to the 13th century and located inside the city walls on the main street of San Gimignano, Via San Matteo, really full historical center and a few steps from the imposing medieval Towers and Cathedral. It offers free WiFi everywhere and features spacious rooms with authentic antique furnishings of the palace, fridge, hairdryer and liquid soaps. A bus stopping 50 metres from Palazzo Buonaccorsi takes guests to Siena and Florence or train station in Poggibonsi. The courtyard is a quiet area for everything.Show full description
This charming and cozy guesthouse in the heart of San Gimignano is a historic palace dating back to the 13th century, providing a unique medieval experience. With a limited number of rooms, it creates an intimate and personalized atmosphere.
Beach front location. Historic. Friendly staff. A jewel of the Tuscan countryside, luxurious Castello delle Serre sits majestically at the top of the charming medieval town of Serre di Rapolano, 40 minutes from Siena and Montepulciano. The hotel has incorporated modern comforts into this grandiose residence which offers oversized beds and spacious marble bathrooms, not to mention a spectacular swimming pool. Picturesque countryside views are the norm as you wander around the beautiful gardens of this exceptional property, perhaps sitting under ancient trees, or lounging in the vast park. The surrounding area offers you all that Tuscany is famous for. Just 4 km away you will find Rapolano Terme, a spa town famous for its healing waters and the Chianti and Montalcino vineyards and wine cellars are nearby, perfect for wine-tasting trips. Unspoilt old hill towns such as San Gimignano and cultural hotspots like Siena, where you can really soak up the art and history of the area are all just a short drive away too.Show full description
Overlooking the surrounding Tuscan countryside, Castello di Montalto offers a free outdoor pool, free WiFi, and free bikes. The property features rustic-style accommodation and a garden with free BBQ facilities. With free private parking, Castello di Montalto is 11 km from the centre of Castelnuovo Berardenga. The apartments come with a living area and a kitchen or kitchenette. Each has a bathroom with a hairdryer and free toiletries, while some also include a private patio or garden. Siena is a 30-minute drive away. The property is 17 minutes' drive from the Thermal Baths in Rapolano Terme, where guests enjoy discounts.Show full description
Romantic. Great views. Located 5 km from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodation with a patio. WiFi is free throughout, and there is also a terrace. Rustic-style apartments at the Querceto all come with a kitchenette, dining area and satellite flat-screen TV. The private bathroom includes a hairdryer and shower. Wine tasting sessions can be organised on site, as well as traditional cooking classes. Guests can enjoy typical Tuscan wine and snacks at the property's wine bar. The property provides free private parking, and is surrounded by olive groves and vineyards. Greve in Chianti is a 20-minute drive away.Show full description
I think this is one of the most PEACEFUL farm stays in Gaiole in Chianti. It also has outstanding views and beautiful surroundings.
Luxurious. Lovely interior design. Borgo San Felice is located in Castelnuovo Berardenga in the heart of the Chianti wine district. It offers spacious rooms with antique furnishings, a swimming pool, and panoramic views. The hotel boasts 2 restaurants. Il Poggio Rosso restaurant offers gourmet cuisine and has a selection of over 500 fine wines. The more informal Osteria del Grigio offers modern Tuscan cuisine and is open for lunch and dinner. There is also a bar on site. In summer, guests can enjoy a drink or a snack by the heated outdoor pool. Bikes are available to rent and you will find a tennis court, gym and bowls court on site. The health centre offers a number of beauty treatments and specialises in wine therapy, massages and other beauty treatments. Rooms here come with air conditioning and satellite TV. Parking is free and free Wi-Fi throughout are available. Borgo San Felice is set on a hill amongst olive groves and vineyards. The local area is full of interesting churches and abbeys, and the town of Siena is just a 30-minute drive away.Show full description
This might be the most luxurious luxury hotel in Gaiole in Chianti.
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